AU2011324958A1 - Indole derivatives - Google Patents

Info

Publication number

AU2011324958A1

AU2011324958A1 AU2011324958A AU2011324958A AU2011324958A1 AU 2011324958 A1 AU2011324958 A1 AU 2011324958A1 AU 2011324958 A AU2011324958 A AU 2011324958A AU 2011324958 A AU2011324958 A AU 2011324958A AU 2011324958 A1 AU2011324958 A1 AU 2011324958A1

Authority

AU

Australia

Prior art keywords

methyl

indol

chloro

oxadiazol

cyclopropyl

Prior art date

2010-11-05

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 150000002475 indoles Chemical class 0.000 title claims abstract description 28
• 229940054051 antipsychotic indole derivative Drugs 0.000 title claims abstract description 11
• 150000001875 compounds Chemical class 0.000 claims description 318
• 238000000034 method Methods 0.000 claims description 179
• -1 2H-tetrazol-5-yl Chemical group 0.000 claims description 173
• WMMGHBYADJNEOC-UHFFFAOYSA-N 3-methoxy-1,2-oxazole-5-carboxylic acid Chemical compound COC=1C=C(C(O)=O)ON=1 WMMGHBYADJNEOC-UHFFFAOYSA-N 0.000 claims description 64
• JQMGTQJLBUOINE-UHFFFAOYSA-N 1-amino-n-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 JQMGTQJLBUOINE-UHFFFAOYSA-N 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 33
• 102000005962 receptors Human genes 0.000 claims description 30
• 108020003175 receptors Proteins 0.000 claims description 30
• 230000003287 optical effect Effects 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• 208000002193 Pain Diseases 0.000 claims description 23
• ZWFYYKVOJQHLTH-UHFFFAOYSA-N 1-[(2,2,2-trifluoroacetyl)amino]cyclopropane-1-carboxylic acid Chemical compound FC(F)(F)C(=O)NC1(C(=O)O)CC1 ZWFYYKVOJQHLTH-UHFFFAOYSA-N 0.000 claims description 22
• 239000000463 material Substances 0.000 claims description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
• 230000036407 pain Effects 0.000 claims description 21
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 20
• 239000004480 active ingredient Substances 0.000 claims description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 239000011570 nicotinamide Substances 0.000 claims description 18
• 229960003966 nicotinamide Drugs 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 14
• 150000001408 amides Chemical class 0.000 claims description 14
• 230000004054 inflammatory process Effects 0.000 claims description 13
• PNXJWEQRIVLWBG-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1C(F)(F)F PNXJWEQRIVLWBG-UHFFFAOYSA-N 0.000 claims description 12
• 206010061218 Inflammation Diseases 0.000 claims description 12
• 101800004538 Bradykinin Proteins 0.000 claims description 11
• QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 11
• QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 10
• 230000002757 inflammatory effect Effects 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 230000005764 inhibitory process Effects 0.000 claims description 9
• OWMVXHFZCCPOTD-UHFFFAOYSA-N 5-cyclopropyl-1,2-oxazole-3-carboxylic acid Chemical compound O1N=C(C(=O)O)C=C1C1CC1 OWMVXHFZCCPOTD-UHFFFAOYSA-N 0.000 claims description 8
• 102000017916 BDKRB1 Human genes 0.000 claims description 8
• 108010044231 Bradykinin B1 Receptor Proteins 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• 230000000694 effects Effects 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• 206010058019 Cancer Pain Diseases 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 201000001119 neuropathy Diseases 0.000 claims description 4
• 230000007823 neuropathy Effects 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 4
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 208000009935 visceral pain Diseases 0.000 claims description 4
• BWGMKKPIGYTTFK-UHFFFAOYSA-N 1-amino-n-[[4-[3,5-dichloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=C(Cl)C=C3C=2Cl)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 BWGMKKPIGYTTFK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 229940104754 Bradykinin B1 receptor antagonist Drugs 0.000 claims description 3
• 208000012514 Cumulative Trauma disease Diseases 0.000 claims description 3
• 208000001640 Fibromyalgia Diseases 0.000 claims description 3
• 201000005569 Gout Diseases 0.000 claims description 3
• 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 3
• 208000030858 Myofascial Pain Syndromes Diseases 0.000 claims description 3
• 208000028990 Skin injury Diseases 0.000 claims description 3
• 239000003144 bradykinin B1 receptor antagonist Substances 0.000 claims description 3
• 208000017169 kidney disease Diseases 0.000 claims description 3
• DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 3
• 201000008482 osteoarthritis Diseases 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 208000017520 skin disease Diseases 0.000 claims description 3
• 230000000392 somatic effect Effects 0.000 claims description 3
• GXGGUTAWKCMRGM-UHFFFAOYSA-N 1-amino-n-[[4-[3-chloro-2-(2-methyltetrazol-5-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound CN1N=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 GXGGUTAWKCMRGM-UHFFFAOYSA-N 0.000 claims description 2
• 208000008035 Back Pain Diseases 0.000 claims description 2
• 208000008930 Low Back Pain Diseases 0.000 claims description 2
• 150000003862 amino acid derivatives Chemical class 0.000 claims description 2
• 238000002156 mixing Methods 0.000 claims description 2
• 235000005152 nicotinamide Nutrition 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• 208000017442 Retinal disease Diseases 0.000 claims 2
• 206010038923 Retinopathy Diseases 0.000 claims 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• ATDUEPWEORQVSN-UHFFFAOYSA-N 1-amino-N-[[4-[3,5-difluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=C(F)C=C3C=2F)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 ATDUEPWEORQVSN-UHFFFAOYSA-N 0.000 claims 1
• MMCPHQGIOZHPNC-UHFFFAOYSA-N 1-amino-N-[[4-[3-chloro-2-(1,3-oxazol-5-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound C=1C=C(N2C3=CC=CC=C3C(Cl)=C2C=2OC=NC=2)C=CC=1CNC(=O)C1(N)CC1 MMCPHQGIOZHPNC-UHFFFAOYSA-N 0.000 claims 1
• NOLZHLVDBFBRBJ-UHFFFAOYSA-N 1-amino-N-[[4-[3-chloro-5-fluoro-2-(2-methyltetrazol-5-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound CN1N=NC(C=2N(C3=CC=C(F)C=C3C=2Cl)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 NOLZHLVDBFBRBJ-UHFFFAOYSA-N 0.000 claims 1
• IPZQNLNTWXRGDL-UHFFFAOYSA-N 1-amino-N-[[4-[3-chloro-5-methoxy-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound ClC=1C2=CC(OC)=CC=C2N(C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)C=1C1=NOC(C)=N1 IPZQNLNTWXRGDL-UHFFFAOYSA-N 0.000 claims 1
• HFGMNVIFDIACNA-UHFFFAOYSA-N 1-amino-N-[[4-[3-cyano-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2C#N)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 HFGMNVIFDIACNA-UHFFFAOYSA-N 0.000 claims 1
• QTVRAOISQPLGGP-UHFFFAOYSA-N 1-amino-N-[[4-[5-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=C(F)C=C3C=2)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 QTVRAOISQPLGGP-UHFFFAOYSA-N 0.000 claims 1
• BMZXVYFAZYAXOI-UHFFFAOYSA-N 1-amino-n-[[4-[3-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)indol-1-yl]phenyl]methyl]cyclopropane-1-carboxamide Chemical compound CC1=NOC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 BMZXVYFAZYAXOI-UHFFFAOYSA-N 0.000 claims 1
• HGYKBJQRRJUYNJ-UHFFFAOYSA-N 2-chloro-n-[1-[[4-[3,5-dichloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]pyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=C(Cl)C=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C(=NC=CC=3)Cl)=CC=2)=N1 HGYKBJQRRJUYNJ-UHFFFAOYSA-N 0.000 claims 1
• RWYFXSVEOCPFJO-UHFFFAOYSA-N 2-chloro-n-[1-[[4-[3-chloro-2-(2-methyltetrazol-5-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]pyridine-3-carboxamide Chemical compound CN1N=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C(=NC=CC=3)Cl)=CC=2)=N1 RWYFXSVEOCPFJO-UHFFFAOYSA-N 0.000 claims 1
• HPHLWAGIPCDPJD-UHFFFAOYSA-N 2-chloro-n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]-2-fluorophenyl]methylcarbamoyl]cyclopropyl]pyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=C(F)C(CNC(=O)C3(CC3)NC(=O)C=3C(=NC=CC=3)Cl)=CC=2)=N1 HPHLWAGIPCDPJD-UHFFFAOYSA-N 0.000 claims 1
• SDLPAZFHDSMFEH-UHFFFAOYSA-N 2-chloro-n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]pyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C(=NC=CC=3)Cl)=CC=2)=N1 SDLPAZFHDSMFEH-UHFFFAOYSA-N 0.000 claims 1
• JZBSMLDTRQQCEQ-UHFFFAOYSA-N 2-chloro-n-[1-[[4-[3-chloro-5-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]pyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=C(F)C=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C(=NC=CC=3)Cl)=CC=2)=N1 JZBSMLDTRQQCEQ-UHFFFAOYSA-N 0.000 claims 1
• QCHQRGSVNBXRCU-UHFFFAOYSA-N 2-fluoro-n-[1-[[4-[5-methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]pyridine-3-carboxamide Chemical compound C=1C2=CC(OC)=CC=C2N(C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C(=NC=CC=3)F)=CC=2)C=1C1=NC(C)=NO1 QCHQRGSVNBXRCU-UHFFFAOYSA-N 0.000 claims 1
• NKVBGKPSZYVYAF-UHFFFAOYSA-N 3-amino-n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]benzamide;hydrochloride Chemical compound Cl.O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(N)C=CC=3)=CC=2)=N1 NKVBGKPSZYVYAF-UHFFFAOYSA-N 0.000 claims 1
• XARSABVGBNNPMH-UHFFFAOYSA-N 3-chloro-1-[4-[[[1-[(2,2,2-trifluoroacetyl)amino]cyclopropanecarbonyl]amino]methyl]phenyl]indole-2-carboxamide Chemical compound NC(=O)C1=C(Cl)C2=CC=CC=C2N1C(C=C1)=CC=C1CNC(=O)C1(NC(=O)C(F)(F)F)CC1 XARSABVGBNNPMH-UHFFFAOYSA-N 0.000 claims 1
• KVNRWAPWFWUMKE-UHFFFAOYSA-N 3-chloro-N-methyl-1-[4-[1-[[1-[(2,2,2-trifluoroacetyl)amino]cyclopropanecarbonyl]amino]ethyl]phenyl]indole-2-carboxamide 1-[(2,2,2-trifluoroacetyl)amino]cyclopropane-1-carboxylic acid Chemical compound FC(C(=O)NC1(CC1)C(=O)O)(F)F.CNC(=O)C=1N(C2=CC=CC=C2C1Cl)C1=CC=C(C=C1)C(C)NC(=O)C1(CC1)NC(C(F)(F)F)=O KVNRWAPWFWUMKE-UHFFFAOYSA-N 0.000 claims 1
• GIADBMXSVVGGLP-UHFFFAOYSA-N 3-methoxy-n-[1-[[5-[2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]pyridin-2-yl]methylcarbamoyl]cyclopropyl]-1,2-oxazole-5-carboxamide Chemical compound O1N=C(OC)C=C1C(=O)NC1(C(=O)NCC=2N=CC(=CC=2)N2C3=CC=CC=C3C=C2C=2N=C(C)ON=2)CC1 GIADBMXSVVGGLP-UHFFFAOYSA-N 0.000 claims 1
• XYLBAHGBFGMKFR-UHFFFAOYSA-N 6-bromo-N-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]pyridine-2-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3N=C(Br)C=CC=3)=CC=2)=N1 XYLBAHGBFGMKFR-UHFFFAOYSA-N 0.000 claims 1
• CYNJYBHGBDSZAQ-UHFFFAOYSA-N C1(CC1)C1=CC(=NO1)C(=O)O.ClC1=C(N(C2=CC=C(C=C12)Cl)C1=CC=C(CNC(=O)C2(CC2)NC(C2=CC(=NC=C2)F)=O)C=C1)C1=NOC(=N1)C Chemical compound C1(CC1)C1=CC(=NO1)C(=O)O.ClC1=C(N(C2=CC=C(C=C12)Cl)C1=CC=C(CNC(=O)C2(CC2)NC(C2=CC(=NC=C2)F)=O)C=C1)C1=NOC(=N1)C CYNJYBHGBDSZAQ-UHFFFAOYSA-N 0.000 claims 1
• DBPKVOXIWVURQD-UHFFFAOYSA-N C=1C=C(N2C3=CC=C(Cl)C=C3C=C2C#N)C=CC=1CNC(=O)C1(N)CC1 Chemical compound C=1C=C(N2C3=CC=C(Cl)C=C3C=C2C#N)C=CC=1CNC(=O)C1(N)CC1 DBPKVOXIWVURQD-UHFFFAOYSA-N 0.000 claims 1
• QFOSLMIDTVRFDN-UHFFFAOYSA-N CC(NC(CO)C(NC1(CC1)C(O)=O)=O)=O.CC1=NC(C(N(C2=CC=CC=C22)C3=CC=C(CNC(C4(CC4)N)=O)C=C3)=C2Cl)=NO1 Chemical compound CC(NC(CO)C(NC1(CC1)C(O)=O)=O)=O.CC1=NC(C(N(C2=CC=CC=C22)C3=CC=C(CNC(C4(CC4)N)=O)C=C3)=C2Cl)=NO1 QFOSLMIDTVRFDN-UHFFFAOYSA-N 0.000 claims 1
• TYSUBRJJUGNXFI-UHFFFAOYSA-N CC1=NC(C(N(C(C2=C3)=CC=C3F)C3=CC=C(CN)C=C3)=C2F)=NO1.COC1=NOC(C(O)=O)=C1 Chemical compound CC1=NC(C(N(C(C2=C3)=CC=C3F)C3=CC=C(CN)C=C3)=C2F)=NO1.COC1=NOC(C(O)=O)=C1 TYSUBRJJUGNXFI-UHFFFAOYSA-N 0.000 claims 1
• STEVUYTUFFFNEJ-UHFFFAOYSA-N CC1=NC(C(N(C2=CC=CC=C22)C3=CC(F)=C(CNC(C4(CC4)N)=O)C=C3)=C2Cl)=NO1.OC(C1(CC1)NC(CC(F)(F)F)=O)=O Chemical compound CC1=NC(C(N(C2=CC=CC=C22)C3=CC(F)=C(CNC(C4(CC4)N)=O)C=C3)=C2Cl)=NO1.OC(C1(CC1)NC(CC(F)(F)F)=O)=O STEVUYTUFFFNEJ-UHFFFAOYSA-N 0.000 claims 1
• JYEDPRRHGKCGET-UHFFFAOYSA-N CC1=NC(C2=CC3=CC=CC=C3N2C2=CC=C(CNC(C3(CC3)N)=O)C=C2)=NO1.COC1=NOC(C(O)=O)=C1 Chemical compound CC1=NC(C2=CC3=CC=CC=C3N2C2=CC=C(CNC(C3(CC3)N)=O)C=C2)=NO1.COC1=NOC(C(O)=O)=C1 JYEDPRRHGKCGET-UHFFFAOYSA-N 0.000 claims 1
• JGRKVVQTHIVVNY-UHFFFAOYSA-N CN1N=CC(=C1)C(=O)O.FC1=C(C(=O)NC2(CC2)C(NCC2=CC=C(C=C2)N2C(=CC3=CC(=CC=C23)F)C2=NOC(=N2)C)=O)C=CC=N1 Chemical compound CN1N=CC(=C1)C(=O)O.FC1=C(C(=O)NC2(CC2)C(NCC2=CC=C(C=C2)N2C(=CC3=CC(=CC=C23)F)C2=NOC(=N2)C)=O)C=CC=N1 JGRKVVQTHIVVNY-UHFFFAOYSA-N 0.000 claims 1
• BJYUOZPBPFPHSV-UHFFFAOYSA-N CN1N=NC(C(N(C(C2=C3)=CC=C3Cl)C3=CC=C(CNC(C4(CC4)N)=O)C=C3)=C2Cl)=N1.OC(C1(CC1)NC(C(F)(F)F)=O)=O Chemical compound CN1N=NC(C(N(C(C2=C3)=CC=C3Cl)C3=CC=C(CNC(C4(CC4)N)=O)C=C3)=C2Cl)=N1.OC(C1(CC1)NC(C(F)(F)F)=O)=O BJYUOZPBPFPHSV-UHFFFAOYSA-N 0.000 claims 1
• KKXNZKDVUFHMDZ-UHFFFAOYSA-N CN1N=NC(C=2N(C3=CC=CC=C3C=2)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 Chemical compound CN1N=NC(C=2N(C3=CC=CC=C3C=2)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 KKXNZKDVUFHMDZ-UHFFFAOYSA-N 0.000 claims 1
• MWDROJDGEYRUQV-UHFFFAOYSA-N COC1=CC=CC(C(=O)NC2(CC2)C(=O)NCC=2C=CC(=CC=2)N2C3=CC=CC=C3C(Cl)=C2C=2N=C(C)ON=2)=C1 Chemical compound COC1=CC=CC(C(=O)NC2(CC2)C(=O)NCC=2C=CC(=CC=2)N2C3=CC=CC=C3C(Cl)=C2C=2N=C(C)ON=2)=C1 MWDROJDGEYRUQV-UHFFFAOYSA-N 0.000 claims 1
• HAVDWLRGYPSYNU-UHFFFAOYSA-N Cn1nnnc1-c1c(Cl)c2ccccc2n1-c1ccc(CN)cc1 Chemical compound Cn1nnnc1-c1c(Cl)c2ccccc2n1-c1ccc(CN)cc1 HAVDWLRGYPSYNU-UHFFFAOYSA-N 0.000 claims 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
• 102100035792 Kininogen-1 Human genes 0.000 claims 1
• BNAKOQLNVSFRIX-UHFFFAOYSA-N N#CC1=C(Cl)C2=CC(OC)=CC=C2N1C(C=C1)=CC=C1CNC(=O)C1(N)CC1 Chemical compound N#CC1=C(Cl)C2=CC(OC)=CC=C2N1C(C=C1)=CC=C1CNC(=O)C1(N)CC1 BNAKOQLNVSFRIX-UHFFFAOYSA-N 0.000 claims 1
• UZKOIQKGQZKYNC-CYBMUJFWSA-N N-[(1R)-1-[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]ethyl]-1-[(2,2,2-trifluoroacetyl)amino]cyclopropane-1-carboxamide Chemical compound N([C@H](C)C=1C=CC(=CC=1)N1C2=CC=CC=C2C(Cl)=C1C=1N=C(C)ON=1)C(=O)C1(NC(=O)C(F)(F)F)CC1 UZKOIQKGQZKYNC-CYBMUJFWSA-N 0.000 claims 1
• RSHOTDNVDUDWGK-OAHLLOKOSA-N N-[1-[[(1R)-1-[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]ethyl]carbamoyl]cyclopropyl]-3-methoxy-1,2-oxazole-5-carboxamide Chemical compound O1N=C(OC)C=C1C(=O)NC1(C(=O)N[C@H](C)C=2C=CC(=CC=2)N2C3=CC=CC=C3C(Cl)=C2C=2N=C(C)ON=2)CC1 RSHOTDNVDUDWGK-OAHLLOKOSA-N 0.000 claims 1
• RTGQLNJJGKABGP-UHFFFAOYSA-N N-[1-[[2-fluoro-4-[5-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-methylpyrazine-2-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=C(F)C=C3C=2)C=2C=C(F)C(CNC(=O)C3(CC3)NC(=O)C=3N=CC(C)=NC=3)=CC=2)=N1 RTGQLNJJGKABGP-UHFFFAOYSA-N 0.000 claims 1
• JWCGVYCUDOLSEU-UHFFFAOYSA-N N-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-1H-pyrazole-4-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C3=CNN=C3)=CC=2)=N1 JWCGVYCUDOLSEU-UHFFFAOYSA-N 0.000 claims 1
• HZVICFKCOLNZGA-UHFFFAOYSA-N N-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-2-methylsulfanylpyrimidine-5-carboxamide Chemical compound C1=NC(SC)=NC=C1C(=O)NC1(C(=O)NCC=2C=CC(=CC=2)N2C3=CC=CC=C3C(Cl)=C2C=2N=C(C)ON=2)CC1 HZVICFKCOLNZGA-UHFFFAOYSA-N 0.000 claims 1
• BVYJNIHRIBCSCN-UHFFFAOYSA-N N-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-methyl-1H-pyrazole-3-carboxamide Chemical compound N1C(C)=CC(C(=O)NC2(CC2)C(=O)NCC=2C=CC(=CC=2)N2C3=CC=CC=C3C(Cl)=C2C=2N=C(C)ON=2)=N1 BVYJNIHRIBCSCN-UHFFFAOYSA-N 0.000 claims 1
• GIRHPDSEIHYCFJ-UHFFFAOYSA-N N-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-methylsulfanylthiophene-2-carboxamide Chemical compound S1C(SC)=CC=C1C(=O)NC1(C(=O)NCC=2C=CC(=CC=2)N2C3=CC=CC=C3C(Cl)=C2C=2N=C(C)ON=2)CC1 GIRHPDSEIHYCFJ-UHFFFAOYSA-N 0.000 claims 1
• RRSIYLWLPRXTKD-UHFFFAOYSA-N N-[1-[[4-[3-chloro-5-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-cyclopropyl-1,2-oxazole-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=C(F)C=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C3=NOC(=C3)C3CC3)=CC=2)=N1 RRSIYLWLPRXTKD-UHFFFAOYSA-N 0.000 claims 1
• XXEAOZXXMNCCDB-UHFFFAOYSA-N N-[1-[[4-[3-chloro-5-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC2(CC2)C(=O)NCC=2C=CC(=CC=2)N2C3=CC=C(F)C=C3C(Cl)=C2C=2N=C(C)ON=2)=N1 XXEAOZXXMNCCDB-UHFFFAOYSA-N 0.000 claims 1
• WOYFZNCABVQFNQ-UHFFFAOYSA-N N-[[4-[3-chloro-5-fluoro-2-(2-methyltetrazol-5-yl)indol-1-yl]phenyl]methyl]-1-[(2,2,2-trifluoroacetyl)amino]cyclopropane-1-carboxamide 3-methoxy-1,2-oxazole-5-carboxylic acid Chemical compound COC1=NOC(=C1)C(=O)O.ClC1=C(N(C2=CC=C(C=C12)F)C1=CC=C(CNC(=O)C2(CC2)NC(C(F)(F)F)=O)C=C1)C=1N=NN(N1)C WOYFZNCABVQFNQ-UHFFFAOYSA-N 0.000 claims 1
• GVTIOBOEEASXQV-UHFFFAOYSA-N N1=CC(=CC2=CC=CC=C12)C(=O)O.ClC1=C(N(C2=CC=CC=C12)C1=CC=C(CNC(=O)C2(CC2)NC(C2=CN=CC=C2)=O)C=C1)C1=NOC(=N1)C Chemical compound N1=CC(=CC2=CC=CC=C12)C(=O)O.ClC1=C(N(C2=CC=CC=C12)C1=CC=C(CNC(=O)C2(CC2)NC(C2=CN=CC=C2)=O)C=C1)C1=NOC(=N1)C GVTIOBOEEASXQV-UHFFFAOYSA-N 0.000 claims 1
• ISCVAFFXJHZRJA-UHFFFAOYSA-N O1C(C)=NC(C=2N(C3=CC=C(F)C=C3C=2C)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 Chemical compound O1C(C)=NC(C=2N(C3=CC=C(F)C=C3C=2C)C=2C=CC(CNC(=O)C3(N)CC3)=CC=2)=N1 ISCVAFFXJHZRJA-UHFFFAOYSA-N 0.000 claims 1
• MFDQNCPWTBMRAY-UHFFFAOYSA-N O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3N=NSC=3)=CC=2)=N1 Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3N=NSC=3)=CC=2)=N1 MFDQNCPWTBMRAY-UHFFFAOYSA-N 0.000 claims 1
• HBYLNRMUIZHMSQ-UHFFFAOYSA-N [4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methanamine Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CN)=CC=2)=N1 HBYLNRMUIZHMSQ-UHFFFAOYSA-N 0.000 claims 1
• FSEGZEZFYKZNFR-UHFFFAOYSA-N [4-[5-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methanamine Chemical compound O1C(C)=NC(C=2N(C3=CC=C(Cl)C=C3C=2)C=2C=CC(CN)=CC=2)=N1 FSEGZEZFYKZNFR-UHFFFAOYSA-N 0.000 claims 1
• STQNELWMBLQANE-UHFFFAOYSA-N methyl 1-[4-[[[1-[(3-methoxy-1,2-oxazole-5-carbonyl)amino]cyclopropanecarbonyl]amino]methyl]phenyl]indole-2-carboxylate Chemical compound COC(=O)C1=CC2=CC=CC=C2N1C(C=C1)=CC=C1CNC(=O)C1(NC(=O)C=2ON=C(OC)C=2)CC1 STQNELWMBLQANE-UHFFFAOYSA-N 0.000 claims 1
• UQLGYNHDSGVILC-UHFFFAOYSA-N methyl 3-chloro-1-[3-fluoro-4-[[[1-[(2,2,2-trifluoroacetyl)amino]cyclopropanecarbonyl]amino]methyl]phenyl]indole-2-carboxylate Chemical compound COC(=O)C1=C(Cl)C2=CC=CC=C2N1C(C=C1F)=CC=C1CNC(=O)C1(NC(=O)C(F)(F)F)CC1 UQLGYNHDSGVILC-UHFFFAOYSA-N 0.000 claims 1
• LSFREYRFGJNXFV-UHFFFAOYSA-N methyl 3-chloro-1-[4-[[[1-[(2,2,2-trifluoroacetyl)amino]cyclopropanecarbonyl]amino]methyl]phenyl]indole-2-carboxylate Chemical compound COC(=O)C1=C(Cl)C2=CC=CC=C2N1C(C=C1)=CC=C1CNC(=O)C1(NC(=O)C(F)(F)F)CC1 LSFREYRFGJNXFV-UHFFFAOYSA-N 0.000 claims 1
• XAHGLJZTVZYSNM-UHFFFAOYSA-N methyl 3-chloro-4-fluoro-1-[4-[[[1-[(2,2,2-trifluoroacetyl)amino]cyclopropanecarbonyl]amino]methyl]phenyl]indole-2-carboxylate Chemical compound COC(=O)C1=C(Cl)C2=C(F)C=CC=C2N1C(C=C1)=CC=C1CNC(=O)C1(NC(=O)C(F)(F)F)CC1 XAHGLJZTVZYSNM-UHFFFAOYSA-N 0.000 claims 1
• PIGAFIPEXTWEES-UHFFFAOYSA-N methyl 3-chloro-4-fluoro-1-[4-[[[1-[(3-methoxy-1,2-oxazole-5-carbonyl)amino]cyclopropanecarbonyl]amino]methyl]phenyl]indole-2-carboxylate Chemical compound COC(=O)C1=C(Cl)C2=C(F)C=CC=C2N1C(C=C1)=CC=C1CNC(=O)C1(NC(=O)C=2ON=C(OC)C=2)CC1 PIGAFIPEXTWEES-UHFFFAOYSA-N 0.000 claims 1
• OTWRGMGYJOZSNH-UHFFFAOYSA-N n-[1-[[2-fluoro-4-[5-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-(trifluoromethyl)pyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=C(F)C=C3C=2)C=2C=C(F)C(CNC(=O)C3(CC3)NC(=O)C=3C=C(C=NC=3)C(F)(F)F)=CC=2)=N1 OTWRGMGYJOZSNH-UHFFFAOYSA-N 0.000 claims 1
• OQPAXRXXJCJKEU-UHFFFAOYSA-N n-[1-[[4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=NOC(C=2N(C3=CC=CC=C3C=2)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(C=NC=3)C(F)(F)F)=CC=2)=N1 OQPAXRXXJCJKEU-UHFFFAOYSA-N 0.000 claims 1
• GRCQOBFZLNGLEI-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(2-methyltetrazol-5-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-2-fluoropyridine-4-carboxamide Chemical compound CN1N=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(F)N=CC=3)=CC=2)=N1 GRCQOBFZLNGLEI-UHFFFAOYSA-N 0.000 claims 1
• NSSHFJSPABJXTM-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(2-methyltetrazol-5-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-fluorobenzamide Chemical compound CN1N=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(F)C=CC=3)=CC=2)=N1 NSSHFJSPABJXTM-UHFFFAOYSA-N 0.000 claims 1
• QBSDNERDSVKPAM-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(2-methyltetrazol-5-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CN1N=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(C=NC=3)C(F)(F)F)=CC=2)=N1 QBSDNERDSVKPAM-UHFFFAOYSA-N 0.000 claims 1
• JTBLHNMUTNYLGN-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-(trifluoromethyl)pyridine-3-carboxamide Chemical compound CC1=NOC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(C=NC=3)C(F)(F)F)=CC=2)=N1 JTBLHNMUTNYLGN-UHFFFAOYSA-N 0.000 claims 1
• VUYPHSFFVXLTDA-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]-2-fluorophenyl]methylcarbamoyl]cyclopropyl]-2-fluoropyridine-4-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=C(F)C(CNC(=O)C3(CC3)NC(=O)C=3C=C(F)N=CC=3)=CC=2)=N1 VUYPHSFFVXLTDA-UHFFFAOYSA-N 0.000 claims 1
• MHTTWOZYEYMDJN-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]-2-fluorophenyl]methylcarbamoyl]cyclopropyl]-3-fluorobenzamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=C(F)C(CNC(=O)C3(CC3)NC(=O)C=3C=C(F)C=CC=3)=CC=2)=N1 MHTTWOZYEYMDJN-UHFFFAOYSA-N 0.000 claims 1
• JCOAXYMQSPMBND-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]-2-fluorophenyl]methylcarbamoyl]cyclopropyl]-5-(trifluoromethyl)pyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=C(F)C(CNC(=O)C3(CC3)NC(=O)C=3C=C(C=NC=3)C(F)(F)F)=CC=2)=N1 JCOAXYMQSPMBND-UHFFFAOYSA-N 0.000 claims 1
• IIKIEBIVFAHKKU-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]-2-fluorophenyl]methylcarbamoyl]cyclopropyl]-5-cyclopropyl-1,2-oxazole-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=C(F)C(CNC(=O)C3(CC3)NC(=O)C3=NOC(=C3)C3CC3)=CC=2)=N1 IIKIEBIVFAHKKU-UHFFFAOYSA-N 0.000 claims 1
• FXMDVEXLSUENOG-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-2-fluoro-5-(trifluoromethyl)benzamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C(=CC=C(C=3)C(F)(F)F)F)=CC=2)=N1 FXMDVEXLSUENOG-UHFFFAOYSA-N 0.000 claims 1
• FTRKTRKAFXWSJT-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-2-fluoropyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C(=NC=CC=3)F)=CC=2)=N1 FTRKTRKAFXWSJT-UHFFFAOYSA-N 0.000 claims 1
• LVKFKGBIAQIQOO-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-2-fluoropyridine-4-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(F)N=CC=3)=CC=2)=N1 LVKFKGBIAQIQOO-UHFFFAOYSA-N 0.000 claims 1
• PVIOSNSFTXHEPS-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-2-methylpyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C(=NC=CC=3)C)=CC=2)=N1 PVIOSNSFTXHEPS-UHFFFAOYSA-N 0.000 claims 1
• IINYVGKBKRWJNH-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-(trifluoromethyl)benzamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(C=CC=3)C(F)(F)F)=CC=2)=N1 IINYVGKBKRWJNH-UHFFFAOYSA-N 0.000 claims 1
• YXHZMTAEXOOTFZ-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-fluoro-4-(trifluoromethyl)benzamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(F)C(=CC=3)C(F)(F)F)=CC=2)=N1 YXHZMTAEXOOTFZ-UHFFFAOYSA-N 0.000 claims 1
• DQVDQRKDGVNBFV-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-fluoro-5-(trifluoromethyl)benzamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=2)=N1 DQVDQRKDGVNBFV-UHFFFAOYSA-N 0.000 claims 1
• IIDVOJSFNXJOHI-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-fluoropyridine-4-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C(=CN=CC=3)F)=CC=2)=N1 IIDVOJSFNXJOHI-UHFFFAOYSA-N 0.000 claims 1
• XWTAGFASMQDLHD-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-iodobenzamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(I)C=CC=3)=CC=2)=N1 XWTAGFASMQDLHD-UHFFFAOYSA-N 0.000 claims 1
• CWHBCVSPBDUMBY-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-methoxy-1,2-oxazole-5-carboxamide Chemical compound O1N=C(OC)C=C1C(=O)NC1(C(=O)NCC=2C=CC(=CC=2)N2C3=CC=CC=C3C(Cl)=C2C=2N=C(C)ON=2)CC1 CWHBCVSPBDUMBY-UHFFFAOYSA-N 0.000 claims 1
• CESGWNHJKPSSCR-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-methylbenzamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(C)C=CC=3)=CC=2)=N1 CESGWNHJKPSSCR-UHFFFAOYSA-N 0.000 claims 1
• QCVDOHCEGXLDQU-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-(trifluoromethyl)pyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(C=NC=3)C(F)(F)F)=CC=2)=N1 QCVDOHCEGXLDQU-UHFFFAOYSA-N 0.000 claims 1
• FLHBWIJVVGVFJQ-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-6-fluoropyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=NC(F)=CC=3)=CC=2)=N1 FLHBWIJVVGVFJQ-UHFFFAOYSA-N 0.000 claims 1
• JPSQOJVPLCDLLB-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-6-methylpyridine-3-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=NC(C)=CC=3)=CC=2)=N1 JPSQOJVPLCDLLB-UHFFFAOYSA-N 0.000 claims 1
• QZTJXSRUSYUOGC-UHFFFAOYSA-N n-[1-[[4-[3-chloro-2-(dimethylcarbamoyl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-methoxy-1,2-oxazole-5-carboxamide Chemical compound O1N=C(OC)C=C1C(=O)NC1(C(=O)NCC=2C=CC(=CC=2)N2C3=CC=CC=C3C(Cl)=C2C(=O)N(C)C)CC1 QZTJXSRUSYUOGC-UHFFFAOYSA-N 0.000 claims 1
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• HRFPYDUIATUYQK-UHFFFAOYSA-N n-[1-[[4-[3-chloro-5-methoxy-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-methoxy-1,2-oxazole-5-carboxamide Chemical compound O1N=C(OC)C=C1C(=O)NC1(C(=O)NCC=2C=CC(=CC=2)N2C3=CC=C(OC)C=C3C(Cl)=C2C=2N=C(C)ON=2)CC1 HRFPYDUIATUYQK-UHFFFAOYSA-N 0.000 claims 1
• OZQSDTAAETYXEX-UHFFFAOYSA-N n-[1-[[4-[5-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-3-methoxy-1,2-oxazole-5-carboxamide Chemical compound O1N=C(OC)C=C1C(=O)NC1(C(=O)NCC=2C=CC(=CC=2)N2C3=CC=C(Cl)C=C3C=C2C=2N=C(C)ON=2)CC1 OZQSDTAAETYXEX-UHFFFAOYSA-N 0.000 claims 1
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• OSAIDWRUVDMYOG-UHFFFAOYSA-N n-[1-[[4-[5-methoxy-2-(5-methyl-1,3,4-oxadiazol-2-yl)indol-1-yl]phenyl]methylcarbamoyl]cyclopropyl]-5-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1C2=CC(OC)=CC=C2N(C=2C=CC(CNC(=O)C3(CC3)NC(=O)C=3C=C(C=NC=3)C(F)(F)F)=CC=2)C=1C1=NN=C(C)O1 OSAIDWRUVDMYOG-UHFFFAOYSA-N 0.000 claims 1
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• OVPAUFDPYOSYHG-UHFFFAOYSA-N n-[[4-[3-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)indol-1-yl]phenyl]methyl]-1-(3,3,3-trifluoropropanoylamino)cyclopropane-1-carboxamide Chemical compound CC1=NOC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)CC(F)(F)F)=CC=2)=N1 OVPAUFDPYOSYHG-UHFFFAOYSA-N 0.000 claims 1
• LMFGQPOKUSLXIQ-UHFFFAOYSA-N n-[[4-[3-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)indol-1-yl]phenyl]methyl]-1-(3,3,3-trifluoropropanoylamino)cyclopropane-1-carboxamide Chemical compound O1C(C)=NC(C=2N(C3=CC=CC=C3C=2Cl)C=2C=CC(CNC(=O)C3(CC3)NC(=O)CC(F)(F)F)=CC=2)=N1 LMFGQPOKUSLXIQ-UHFFFAOYSA-N 0.000 claims 1
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